Stereoselective synthesis of substituted bicyclo- 3.3.1 -nonan-9-ones by additions of enamines of cyclohexanones to 4-ethoxy-1,1,1-trifluorobut-3-ene-2-one
Stereoselective synthesis of substituted bicyclo- 3.3.1 -nonan-9-ones by additions of enamines of cyclohexanones to 4-ethoxy-1,1,1-trifluorobut-3-ene-2-one
Addition of the pyrrolidine enamine of cyclohexanone to 4-ethoxy-1,1,1-trifluorobut-3-ene-2-one affords a single diastereoisomer of 4-ethoxy-2-hydroxy-2-trifluoromethylbicyclo [3.3.1]nonan-9-one. Similarly the pyrrolidine enamine of 4-methylcyclohexanone also in a highly diastereoselective manner affords a single bicyclic ketone. In the latter case a single crystal X-ray diffraction analysis permits unambiguous determination of all stereochemical detail. Other examples of addition to 4-ethoxy-1,1,1-trifluorobut-3-ene-2-one are discussed. The mechanistic explanation of the unusually high selectivity is discussed.
addition, enamines, organofluorine, phenols, x-ray diffraction
trifluoromethyl ketones, efficient synthesis
7255-7260
Andrew, R. J.
004eed6c-6a89-451a-9cd1-8e27ce59c9e4
Mellor, J. M.
d9b993ad-31be-4f91-8ea3-1723cd1c23bc
Reid, G.
ff85ed93-1d4e-4c2b-a9b7-d927a61c4abe
8 September 2000
Andrew, R. J.
004eed6c-6a89-451a-9cd1-8e27ce59c9e4
Mellor, J. M.
d9b993ad-31be-4f91-8ea3-1723cd1c23bc
Reid, G.
ff85ed93-1d4e-4c2b-a9b7-d927a61c4abe
Andrew, R. J., Mellor, J. M. and Reid, G.
(2000)
Stereoselective synthesis of substituted bicyclo- 3.3.1 -nonan-9-ones by additions of enamines of cyclohexanones to 4-ethoxy-1,1,1-trifluorobut-3-ene-2-one.
Tetrahedron, 56 (37), .
(doi:10.1016/S0040-4020(00)00596-2).
Abstract
Addition of the pyrrolidine enamine of cyclohexanone to 4-ethoxy-1,1,1-trifluorobut-3-ene-2-one affords a single diastereoisomer of 4-ethoxy-2-hydroxy-2-trifluoromethylbicyclo [3.3.1]nonan-9-one. Similarly the pyrrolidine enamine of 4-methylcyclohexanone also in a highly diastereoselective manner affords a single bicyclic ketone. In the latter case a single crystal X-ray diffraction analysis permits unambiguous determination of all stereochemical detail. Other examples of addition to 4-ethoxy-1,1,1-trifluorobut-3-ene-2-one are discussed. The mechanistic explanation of the unusually high selectivity is discussed.
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Published date: 8 September 2000
Keywords:
addition, enamines, organofluorine, phenols, x-ray diffraction
trifluoromethyl ketones, efficient synthesis
Identifiers
Local EPrints ID: 18905
URI: http://eprints.soton.ac.uk/id/eprint/18905
ISSN: 0040-4020
PURE UUID: 2482d911-17ff-445e-9d07-58eaf7503dea
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Date deposited: 16 Dec 2005
Last modified: 15 Mar 2024 06:09
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Author:
R. J. Andrew
Author:
J. M. Mellor
Author:
G. Reid
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